Hydrazine hydrate (1:1) → HCID 178432089, compound

HRID 1530110Notes

Reaction equation

HRID 1530110 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28]([NH2:30])=O)=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[NH2:32]N.COC(OC)[N:37]([CH3:39])C>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:17]4[S:18][C:19]([C:28]5[N:30]=[CH:39][NH:37][N:32]=5)=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:14]([CH3:16])[N:15]=3)[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 66855664HCID 66855664, compound

Product 1

HCID 178432089HCID 178432089, compound

Conditions

Temperature
100 °C

Procedure

A suspension of 2-(6-cyclohexyl-2-methylimidazo[1,2-a]pyridin-3-yl)-4-phenyl-1,3-thiazole-5-carboxamide (104 mg, 0.25 mmol) obtained above in N,N-dimethylformamide dimethylacetal (20 mL) was stirred at 100° C. for 12 h. The reaction mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was suspended in AcOH (5 mL), and then was added hydrazine monohydrate (70 μL, 1.4 mmol) at 0° C., and the mixture was stirred at 90° C. for 1 h, allowed to cool to rt, and then concentrated under reduced pressure. The residue was diluted with EtOAc (20 mL), water (10 mL) and saturated aqueous solution of sodium bicarbonate (10 mL), and the aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (30 mL). The combined organic layers were dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure.

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated under reduced pressure
  3. stirringthe mixture was stirred at 90° C. for 1 h
  4. temperatureto cool to rt
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with EtOAc (20 mL), water (10 mL) and saturated aqueous solution of sodium bicarbonate (10 mL)
  7. extractionthe aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (30 mL)
  8. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  9. customInsoluble materials were removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-732e3e50b8d940dc897ca4ac9daf718b
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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